A Perfectionist’s Guide to Clicking Send
In January 2014, I channeled my creative life force into launching a new app. Three months later, 250K people were signing up every day. Three months after that we had 15M users, a team of 35, and had raised $35M in capital. At the age of 31, I felt like I finally had the breakthrough that I was waiting for.
After that venture ended, I kept building, but something had changed. I became highly critical of my own work, believing the next thing I release publicly needs to be as big of a hit. Nothing I built ever saw the light of day. I suffered from feelings of anxiety, self-doubt, which distanced me from the very community that embraced me. I became overly pedantic with details, which made me hard to work with, affected my relationships, and limited my growth as a leader.
This carried on for years and seeped into my most recent startup, where we built several novel and interesting social concepts that never launched. One of our concepts, Fave, was eventually launched by another team to great success (kudos to Locket).
After some introspection, my co-founder and I identified that our drive for perfection was detrimental on many fronts and set out to change our patterns. As a recovering perfectionist, I wanted to share what I’ve learned in hopes of helping others who might be suffering from perfectionism
Perfection Borrows Against Progress
I’ve gone through several difficult moments in my professional career that I can now attribute to my perfectionist behavior. My deep-seated fear of rejection or humiliation, which likely stemmed from being bullied when I young, manifested in a strong desire to present without flaw.
In my experience, the impact of this protective mindset can limit effectiveness in a number of ways:
- Need for constant reassurance and approval from others
- Fear of taking risks or trying something new
- Difficulty in delegating tasks to others
- Obsessing over small details and losing sight of the bigger picture
- Tendency to procrastinate due to fear of failure
- All-or-nothing approach to tasks and goals
Perfectionism is the voice of the oppressor — Anne Lamott
The thing is, in order to make progress and find success in life, we need to be able to take risks and put our trust in others. Perfectionist behaviors stand squarely in the way of doing that. The pursuit of perfection can be masked as a heroic act, protecting some sort of standard of quality, when in reality it’s a shield that we’re hiding behind, and not the sword we think we’re wielding.
Taking risks and building relationships requires making ourselves vulnerable, stepping outside of our comfort zone, and being open to the possibility of failure and rejection. Putting down our shield is the gateway to growth. It’s going to be uncomfortable, but here are some great strategies to help lean into this edge.
Escaping the Prison of Perfectionism
Overcoming perfectionism is a practice of letting go of control and placing your trust into the world around you. Instead of operating from a protective, defensive mind — we want to shift to an expansive, abundant mindset.
Below are some strategies I’ve learned through my own process or books. Putting these into practice have really made a difference in how I relate to my work and others, and has been reflected in the positive change in the recent feedback from my peers compared to a few years ago.
1. Share incomplete work, often
The more time we invest into a task, the stronger our emotional attachment to it becomes. This attachment can motivate us to put in extra effort and strive for excellence, but at the same time, we may lose perspective and objectivity, making it difficult to identify potential flaws or areas for improvement. This can lead to missed deadlines, poor-quality work, or even damage to our personal and professional reputation.
By sharing unfinished work, however, we can invite feedback from others who can help refine our ideas and provide fresh perspectives. If we wait until the project is complete before sharing it, we risk finding out that we have missed key requirements or made mistakes that could have been avoided if caught earlier. By sharing work in progress, we can get input from stakeholders along the way, identify and address any issues, and ensure that we are on track to meet project goals.
For instance, as a musician, sending a friend a barebones musical idea can spark their creativity, allowing them to add a unique vocal line or guitar riff that adds a fresh perspective to the track. As opposed to sharing a finished product, which leaves less room for input and positions the recipient more as a critic.
2. Celebrate your mistakes and failures
It may sound odd, but treating failures as a good thing is an essential step in overcoming perfectionism because it allows us to reframe our perception of “mistakes” as opportunities for growth, rather than seeing them as a reflection of our inadequacy or evidence of our shortcomings.
Here are some examples of what celebrating failures might look like:
- Reflect on what you learned: Instead of dwelling on the negative aspects of a failure, take some time to reflect on what you learned from the experience. Document the insights or new knowledge you gained, and think about how you can apply these lessons in the future.
- Fail forward: Instead of hiding or avoiding it, step up and humbly share the mistake with your peers. Take the initiative to drive a process around extracting as many learnings from the situation as possible. It’s not about placing blame, it’s about being accountable and exercising leadership. Showing up like this can build trust and inspire others to do the same.
- Use humor to diffuse the tension: Sometimes, the best way to cope with a failure is to find the humor in the situation. Laughing at yourself and your mistakes can help you put things in perspective and reduce the pressure to be perfect. Turn the failure into a meme, gif, or sticker on Slack. Fail gloriously.
What are some other ways we can celebrate our mistakes? Drop a comment below and share your story.
Humility is important in a leader and role model. When you succeed, speak about it softly or let others mention it for you. But when you make a mistake, say it clearly and loudly so that everyone can learn and profit from your errors. In other words “Whisper wins and shout mistakes” — Reed Hastings, No Rules Rules
3. Give others the room to fail
Practicing self-compassion can be challenging, but starting with compassion for others can be easier. Holding ourselves to high standards can make us critical of both ourselves and others.
When we see someone’s work and our initial reaction is negative, it’s a great opportunity to practice compassion, curiosity, and gratitude. If it’s a friend, we could say, “I think it’s awesome that you’re putting yourself out there, how’d you make that?”. If it’s a co-worker, we can thank them for their effort and ask them to walk us through their thinking to help them self-identify opportunities for improvement.
By creating a safe space for others to fail and make mistakes, we allow them to learn and grow just as we do. By leaving the control in their hands, we remain in a supporting role. In turn, we build more trust with our peers and improve our relationships. As we increase our compassion for others, we also begin to notice a shift our relationship with ourself.
4. Practice daily affirmations
Affirmations are positive statements, spoken aloud to ourself, that can help overcome self-sabotaging and negative thoughts, which are common in perfectionists. When we repeat them often, and believe in them, we can start to make positive changes. By increasing the volume of the positive voices in our internal dialog, affirmations can create a lasting shift in our mindset, emotions, and overall well-being.
You might feel silly the first few times you do this, but after a week or so you’ll start to notice subtle shifts in your mood and thought patterns. Think of it like creating your own mantra. Cliché affirmations like “I am loved” can be helpful, but what’s more effective is to tailor your affirmations to say the direct opposite of your loudest saboteurs.
Here are a few examples of counter-affirmations:
Negative: No one is going to read my writing
Affirmations: I am a writer / I have interesting ideas / I enjoy writing
Negative: I am unloveable
Affirmation: My parents love me / My friends love me / I love myself
Negative: All I do is fail
Affirmation: I am not the sum of my failures / I am proud of myself / I am successful
Building new habits can be hard, but starting small makes them easy. Start with just a few affirmations and practice them every morning. Once you build the habit, you can expand your set of affirmations. Read more on the benefits and how to start your daily affirmations.
Practice Makes Purpose
Making mistakes is a natural and necessary part of the learning process for every human. It’s uncomfortable to open ourselves up to failure, but if we can truly embrace failure as a part of the process and not a reflection of our value or identity, we can become lighter, more playful, and more empathetic in the challenging situations we encounter.
We have to put the reps in. By practicing humility, self-love, and putting trust in others time and time again, that’s when we start to shift our belief structure and value a new way of living.
Go forth and embrace imperfection!
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Side Quests
- Positive Intelligence: Research-based tools for cultivating positivity
- Miracle Morning: Great book where I learned about affirmations
- No Rules Rules: Netflix CEO’s book on innovation mindset
